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The asymmetric unit of the title compound, C8H7NO5, contains two crystallographically independent mol­ecules. In both mol­ecules, an intramolecular hydrogen bond exists between the hydroxyl group and the O atom of the carbonyl group. The mol­ecules are stacked, with weak π–π interactions, along the a axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805008627/ci6550sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805008627/ci6550Isup2.hkl
Contains datablock I

CCDC reference: 270275

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.054
  • wR factor = 0.152
  • Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT (Bruker, 2001); software used to prepare material for publication: SHELXTL-NT.

Methyl 5-nitrosalicylate top
Crystal data top
C8H7NO5F(000) = 816.0
Mr = 197.15Dx = 1.538 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1515 reflections
a = 6.9648 (12) Åθ = 2.7–24.1°
b = 13.162 (2) ŵ = 0.13 mm1
c = 18.579 (3) ÅT = 293 K
β = 91.015 (4)°Prism, colourless
V = 1702.9 (5) Å30.30 × 0.20 × 0.18 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
3689 independent reflections
Radiation source: fine-focus sealed tube2100 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
φ and ω scansθmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 88
Tmin = 0.964, Tmax = 0.973k = 1516
9850 measured reflectionsl = 1223
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0703P)2]
where P = (Fo2 + 2Fc2)/3
3689 reflections(Δ/σ)max = 0.001
263 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.17 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.3603 (3)0.91571 (18)0.13124 (10)0.0645 (6)
N20.8628 (3)0.83944 (15)0.41184 (11)0.0585 (5)
O10.3617 (2)0.79811 (12)0.38891 (8)0.0674 (5)
O20.3701 (3)0.93695 (13)0.45580 (9)0.0819 (6)
O30.3923 (3)1.11376 (14)0.39449 (10)0.0762 (6)
O40.3692 (3)0.96760 (15)0.07717 (10)0.1005 (7)
O50.3474 (3)0.82363 (16)0.12910 (10)0.0969 (7)
O60.8419 (3)0.75515 (14)0.38619 (10)0.0923 (7)
O70.8768 (3)0.85342 (14)0.47634 (10)0.0914 (7)
O80.8958 (3)1.17718 (13)0.23490 (10)0.0732 (6)
O90.8889 (3)1.05475 (14)0.12485 (9)0.0823 (6)
O100.8523 (3)0.88890 (13)0.14417 (9)0.0728 (5)
C10.3707 (3)0.95549 (15)0.32950 (11)0.0449 (5)
C20.3831 (3)1.06224 (17)0.33271 (13)0.0535 (6)
C30.3876 (3)1.11795 (18)0.26907 (14)0.0632 (7)
H3A0.39611.18840.27120.076*
C40.3797 (3)1.07114 (18)0.20371 (13)0.0603 (6)
H4A0.38221.10910.16150.072*
C50.3681 (3)0.96631 (17)0.20107 (11)0.0510 (6)
C60.3623 (3)0.90819 (16)0.26266 (11)0.0463 (5)
H60.35280.83780.25950.056*
C70.3676 (3)0.89711 (17)0.39703 (11)0.0497 (6)
C80.3629 (4)0.73781 (18)0.45503 (12)0.0757 (8)
H8A0.47100.75700.48480.114*
H8B0.37180.66700.44320.114*
H8C0.24640.74990.48060.114*
C90.8764 (3)0.99483 (16)0.24499 (11)0.0458 (5)
C100.8878 (3)1.09296 (16)0.27507 (12)0.0514 (6)
C110.8883 (3)1.10505 (17)0.34957 (12)0.0577 (6)
H110.89421.17000.36920.069*
C120.8803 (3)1.02286 (17)0.39407 (12)0.0544 (6)
H120.88111.03110.44380.065*
C130.8708 (3)0.92712 (15)0.36378 (11)0.0454 (5)
C140.8689 (3)0.91220 (15)0.29068 (12)0.0467 (5)
H140.86260.84670.27200.056*
C150.8745 (3)0.98373 (19)0.16611 (13)0.0555 (6)
C160.8474 (4)0.8721 (2)0.06650 (13)0.0883 (9)
H16A0.75390.91640.04450.132*
H16B0.81350.80280.05670.132*
H16C0.97170.88620.04730.132*
H30.388 (5)1.069 (2)0.4309 (19)0.136 (14)*
H80.902 (4)1.158 (2)0.1896 (17)0.120 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0773 (15)0.0812 (16)0.0350 (12)0.0026 (11)0.0001 (10)0.0028 (11)
N20.0693 (14)0.0536 (13)0.0528 (13)0.0006 (9)0.0073 (11)0.0013 (11)
O10.1074 (14)0.0591 (10)0.0356 (9)0.0026 (9)0.0047 (9)0.0047 (8)
O20.1318 (17)0.0752 (12)0.0388 (10)0.0126 (10)0.0005 (10)0.0058 (9)
O30.1115 (16)0.0604 (11)0.0568 (12)0.0107 (10)0.0090 (11)0.0152 (10)
O40.1540 (19)0.1079 (16)0.0398 (10)0.0116 (13)0.0030 (12)0.0149 (11)
O50.158 (2)0.0837 (14)0.0486 (12)0.0169 (13)0.0029 (12)0.0124 (11)
O60.154 (2)0.0583 (11)0.0651 (12)0.0159 (11)0.0112 (12)0.0027 (10)
O70.156 (2)0.0772 (13)0.0506 (11)0.0038 (11)0.0005 (12)0.0053 (10)
O80.1134 (16)0.0516 (10)0.0544 (12)0.0020 (9)0.0003 (11)0.0046 (9)
O90.1288 (16)0.0740 (12)0.0438 (10)0.0050 (11)0.0058 (10)0.0049 (10)
O100.1068 (14)0.0686 (11)0.0428 (10)0.0058 (9)0.0072 (9)0.0144 (9)
C10.0438 (12)0.0520 (13)0.0389 (12)0.0001 (9)0.0013 (9)0.0014 (10)
C20.0535 (14)0.0573 (14)0.0497 (14)0.0027 (10)0.0031 (11)0.0029 (12)
C30.0703 (17)0.0537 (14)0.0656 (17)0.0013 (11)0.0033 (14)0.0048 (13)
C40.0643 (16)0.0645 (16)0.0522 (15)0.0033 (11)0.0050 (12)0.0177 (12)
C50.0476 (13)0.0649 (15)0.0405 (13)0.0010 (10)0.0016 (10)0.0036 (11)
C60.0469 (13)0.0521 (12)0.0398 (12)0.0015 (9)0.0004 (10)0.0023 (10)
C70.0526 (14)0.0603 (15)0.0362 (13)0.0045 (10)0.0030 (10)0.0057 (11)
C80.115 (2)0.0686 (17)0.0438 (14)0.0064 (14)0.0066 (14)0.0158 (13)
C90.0451 (12)0.0516 (12)0.0405 (12)0.0049 (9)0.0013 (9)0.0041 (10)
C100.0578 (15)0.0474 (13)0.0491 (14)0.0025 (10)0.0010 (11)0.0001 (11)
C110.0786 (17)0.0458 (13)0.0486 (14)0.0030 (11)0.0001 (12)0.0150 (11)
C120.0631 (15)0.0582 (14)0.0418 (13)0.0039 (11)0.0012 (11)0.0066 (11)
C130.0456 (13)0.0487 (12)0.0419 (12)0.0002 (9)0.0010 (10)0.0020 (10)
C140.0503 (13)0.0454 (12)0.0444 (13)0.0003 (9)0.0017 (10)0.0066 (10)
C150.0585 (15)0.0608 (15)0.0469 (14)0.0055 (11)0.0046 (11)0.0043 (12)
C160.121 (2)0.099 (2)0.0443 (15)0.0131 (17)0.0104 (16)0.0254 (15)
Geometric parameters (Å, º) top
O1—C71.312 (3)C6—H60.93
O1—C81.462 (3)C14—H140.93
O2—C71.211 (2)C5—C41.383 (3)
C1—C61.390 (3)C5—N11.459 (3)
C1—C21.409 (3)O4—N11.217 (2)
C1—C71.472 (3)O3—C21.334 (3)
C13—C141.372 (3)O3—H30.89 (3)
C13—C121.381 (3)C11—C101.393 (3)
C13—N21.461 (3)C11—H110.93
O9—C151.214 (3)C2—C31.392 (3)
C12—C111.363 (3)C4—C31.362 (3)
C12—H120.93C4—H4A0.93
C9—C141.381 (3)C3—H3A0.93
C9—C101.409 (3)C8—H8A0.96
C9—C151.473 (3)C8—H8B0.96
O5—N11.216 (2)C8—H8C0.96
O10—C151.321 (3)C16—H16A0.96
O10—C161.460 (3)C16—H16B0.96
O8—C101.338 (3)C16—H16C0.96
O8—H80.88 (3)O7—N21.215 (2)
C6—C51.378 (3)N2—O61.215 (2)
C7—O1—C8116.27 (18)C12—C11—H11119.6
C6—C1—C2119.1 (2)C10—C11—H11119.6
C6—C1—C7121.80 (19)O3—C2—C3117.5 (2)
C2—C1—C7119.1 (2)O3—C2—C1123.1 (2)
C14—C13—C12122.2 (2)C3—C2—C1119.5 (2)
C14—C13—N2119.48 (18)O8—C10—C11117.4 (2)
C12—C13—N2118.28 (19)O8—C10—C9122.7 (2)
O2—C7—O1122.2 (2)C11—C10—C9119.9 (2)
O2—C7—C1122.8 (2)C3—C4—C5119.0 (2)
O1—C7—C1114.9 (2)C3—C4—H4A120.5
C11—C12—C13118.6 (2)C5—C4—H4A120.5
C11—C12—H12120.7C4—C3—C2121.2 (2)
C13—C12—H12120.7C4—C3—H3A119.4
C14—C9—C10118.7 (2)C2—C3—H3A119.4
C14—C9—C15122.25 (19)O1—C8—H8A109.5
C10—C9—C15119.0 (2)O1—C8—H8B109.5
C15—O10—C16116.6 (2)H8A—C8—H8B109.5
C10—O8—H8108 (2)O1—C8—H8C109.5
C5—C6—C1119.5 (2)H8A—C8—H8C109.5
C5—C6—H6120.3H8B—C8—H8C109.5
C1—C6—H6120.3O10—C16—H16A109.5
C13—C14—C9119.72 (19)O10—C16—H16B109.5
C13—C14—H14120.1H16A—C16—H16B109.5
C9—C14—H14120.1O10—C16—H16C109.5
C6—C5—C4121.8 (2)H16A—C16—H16C109.5
C6—C5—N1119.0 (2)H16B—C16—H16C109.5
C4—C5—N1119.2 (2)O7—N2—O6122.2 (2)
O9—C15—O10122.9 (2)O7—N2—C13118.7 (2)
O9—C15—C9123.5 (2)O6—N2—C13119.2 (2)
O10—C15—C9113.6 (2)O5—N1—O4122.5 (2)
C2—O3—H3109 (2)O5—N1—C5119.1 (2)
C12—C11—C10120.8 (2)O4—N1—C5118.4 (2)
C8—O1—C7—O21.4 (3)C6—C1—C2—O3179.8 (2)
C8—O1—C7—C1178.7 (2)C7—C1—C2—O30.0 (3)
C6—C1—C7—O2178.1 (2)C6—C1—C2—C30.3 (3)
C2—C1—C7—O22.1 (3)C7—C1—C2—C3179.5 (2)
C6—C1—C7—O11.8 (3)C12—C11—C10—O8179.9 (2)
C2—C1—C7—O1178.05 (18)C12—C11—C10—C90.8 (3)
C14—C13—C12—C110.1 (3)C14—C9—C10—O8179.9 (2)
N2—C13—C12—C11179.85 (19)C15—C9—C10—O80.4 (3)
C2—C1—C6—C50.6 (3)C14—C9—C10—C111.0 (3)
C7—C1—C6—C5179.16 (19)C15—C9—C10—C11179.5 (2)
C12—C13—C14—C90.1 (3)C6—C5—C4—C30.7 (3)
N2—C13—C14—C9179.95 (18)N1—C5—C4—C3179.8 (2)
C10—C9—C14—C130.6 (3)C5—C4—C3—C20.3 (4)
C15—C9—C14—C13179.92 (19)O3—C2—C3—C4179.7 (2)
C1—C6—C5—C40.8 (3)C1—C2—C3—C40.2 (4)
C1—C6—C5—N1179.63 (19)C14—C13—N2—O7175.4 (2)
C16—O10—C15—O90.6 (3)C12—C13—N2—O74.6 (3)
C16—O10—C15—C9179.5 (2)C14—C13—N2—O64.7 (3)
C14—C9—C15—O9176.8 (2)C12—C13—N2—O6175.3 (2)
C10—C9—C15—O92.6 (3)C6—C5—N1—O50.6 (3)
C14—C9—C15—O104.2 (3)C4—C5—N1—O5179.0 (2)
C10—C9—C15—O10176.30 (18)C6—C5—N1—O4178.7 (2)
C13—C12—C11—C100.2 (3)C4—C5—N1—O41.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.89 (3)1.81 (3)2.597 (3)146 (3)
O8—H8···O90.88 (3)1.82 (3)2.603 (2)147 (3)
 

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